Polyacetylenes from the roots of Panax ginseng

Anticarcinogenic Effect of Panax ginseng C.A. Meyer and Identification of Active Compounds

“…The polysaccharide revealed anticomplementary activity (64,65), reticuloendothelial system-potentiating activity, alkaline phosphatase-inducing activity (66), and cytoprotective activity (67,68). Lately, various polyacetylenes extracted from ginseng (69,70) are known to have cytotoxic activity (71).…”

An alternative and convenient synthesis of oct-7-enal, a naturally-occurring aldehyde isolated from the Japanese thistle Cirsium dipsacolepis

“…Spectral data of the synthetic compound were in agreement with the literature. 7 In conclusion, an alternative and simple synthesis of the natural product oct-7-enal (8) was achieved in five steps and 38% overall yield, from commercially available pentane-1,5-diol. The synthesis involved differential protection of both hydroxyl groups of the diol with inclusion of a suitable leaving group, which after copper (I)-assisted displacement with an allyl Grignard furnished the required 8-carbon chain.…”

“…5 Known as yamagobo, this is a perennial herb that grows in Japan on dry plains, which is the source of bioactive compounds 6 and which edible roots, once pickled, are used to accompany meat-based foods due to their extraordinary flavor. The unsaturated aldehyde has been synthesized in widely different scales and diverse purposes, by dihydroxylation of one of the double bonds of 1,8-nonadiene, followed by oxidative fission of the resulting diol, 7,8 as well as by partial hydroboration-oxidation and further oxidation of 1,7-octadiene 9 and biochemical oxidation of this diene with Pseudomonas oleovorans monooxygenase. 10 Also, copper (I) and lead (IV)-catalyzed oxidative ring opening of cyclooctanol 11 were employed for its synthesis, as well as copper (I)-assisted conjugate addition of 4-pentenylmagnesium bromide to acrolein diethyl acetal, followed by acid hydrolysis of the resulting enol ether, 12 isomerization of cyclooctene oxide employing solid acids and bases, 13 and isomerization of 2,7-octadien-1-ol on copper, chromium and zinc composite catalysts at 180-250 ºC 14 or on a copper catalyst.…”

“…10 Also, copper (I) and lead (IV)-catalyzed oxidative ring opening of cyclooctanol 11 were employed for its synthesis, as well as copper (I)-assisted conjugate addition of 4-pentenylmagnesium bromide to acrolein diethyl acetal, followed by acid hydrolysis of the resulting enol ether, 12 isomerization of cyclooctene oxide employing solid acids and bases, 13 and isomerization of 2,7-octadien-1-ol on copper, chromium and zinc composite catalysts at 180-250 ºC 14 or on a copper catalyst. 15 However, these approaches are not exempt from serious drawbacks, such as low yields, 7 use of harsh conditions, 13,14 requirement of expensive starting materials, 7,10,12 use of special or not readily available catalysts or co-factors, 10 inconvenient separation conditions, 14 such as preparative HPLC, 7 and the concomitant production of unwanted byproducts, 13 sometimes the aldehyde 8 being only a minor product. 11 The reactivity of 8 as a model in the selective reduction of carbonyls, mediated by 2-propanol in supercritical fluids, has been studied.…”

Antimicrobial Polyacetylenes from Panax ginseng Hairy Root Culture

“…The roots of P. ginseng have been used in traditional medicine in Japan, China, and Korea and are known for their tonic effect. A series of triterpenoid saponins [1][2][3][4][5][6][7][8] and polyacetylenes [9][10][11][12][13][14][15][16] have been isolated previously from this plant. To produce ginseng saponins, callus, tissue culture and hairy root culture were established.…”